JPH0641212A - アニオン重合調節剤 - Google Patents

アニオン重合調節剤

Info

Publication number: JPH0641212A
Authority: JP; Japan
Prior art keywords: compound; ether; compounds; initiator; organic
Prior art date: 1992-04-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP5077873A

Other languages

English (en)

Japanese (ja)

Inventor

Wen-Liang Hsu

ウエン−リャン・ス

Adel F Halasa

アデル・ファーハン・ハラサ

Barry A Matrana

バリー・アレン・マトラナ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-04-06

Filing date

1993-04-05

Publication date

1994-02-15

1993-04-05 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1994-02-15 Publication of JPH0641212A publication Critical patent/JPH0641212A/ja

Status Pending legal-status Critical Current

Links

239000003607 modifier Substances 0.000 title claims description 18
238000010539 anionic addition polymerization reaction Methods 0.000 title description 2
239000000178 monomer Substances 0.000 claims abstract description 52
150000001875 compounds Chemical class 0.000 claims abstract description 49
229920000642 polymer Polymers 0.000 claims abstract description 37
239000003999 initiator Substances 0.000 claims abstract description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 20
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 20
229920001195 polyisoprene Polymers 0.000 claims abstract description 18
239000003054 catalyst Substances 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
239000003960 organic solvent Substances 0.000 claims abstract description 8
-1 alkyl tetrahydrofurfuryl ether Chemical compound 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
IEOPZUMPHCZMCS-UHFFFAOYSA-N 2-(methoxymethyl)oxolane Chemical group COCC1CCCO1 IEOPZUMPHCZMCS-UHFFFAOYSA-N 0.000 claims description 17
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 17
125000001979 organolithium group Chemical group 0.000 claims description 12
150000002900 organolithium compounds Chemical class 0.000 claims description 9
229920001971 elastomer Polymers 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 5
VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 claims description 4
150000001553 barium compounds Chemical class 0.000 claims description 4
150000002901 organomagnesium compounds Chemical class 0.000 claims description 4
PGZISVXTYZWYPK-UHFFFAOYSA-N 2-(butoxymethyl)oxolane Chemical compound CCCCOCC1CCCO1 PGZISVXTYZWYPK-UHFFFAOYSA-N 0.000 claims description 3
230000002194 synthesizing effect Effects 0.000 claims description 3
KOJGQOMKJLGGPI-UHFFFAOYSA-N 2-(propoxymethyl)oxolane Chemical compound CCCOCC1CCCO1 KOJGQOMKJLGGPI-UHFFFAOYSA-N 0.000 claims description 2
238000007334 copolymerization reaction Methods 0.000 claims 1
150000002642 lithium compounds Chemical class 0.000 claims 1
150000002681 magnesium compounds Chemical class 0.000 claims 1
150000003112 potassium compounds Chemical class 0.000 claims 1
150000003388 sodium compounds Chemical class 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 39
230000000379 polymerizing effect Effects 0.000 abstract description 4
150000001993 dienes Chemical class 0.000 description 37
229920002554 vinyl polymer Polymers 0.000 description 28
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 27
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 19
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 17
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 11
229930195733 hydrocarbon Natural products 0.000 description 11
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
150000002430 hydrocarbons Chemical class 0.000 description 10
150000001491 aromatic compounds Chemical class 0.000 description 9
229920001577 copolymer Polymers 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
229920003048 styrene butadiene rubber Polymers 0.000 description 7
239000004215 Carbon black (E152) Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000007822 coupling agent Substances 0.000 description 6
239000002879 Lewis base Substances 0.000 description 5
239000005062 Polybutadiene Substances 0.000 description 5
150000007527 lewis bases Chemical class 0.000 description 5
229920002857 polybutadiene Polymers 0.000 description 5
239000005060 rubber Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000002524 organometallic group Chemical group 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000002174 Styrene-butadiene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003505 polymerization initiator Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DQFAIOJURQGXBT-UHFFFAOYSA-N 1,2,4-tris(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C(C=C)=C1 DQFAIOJURQGXBT-UHFFFAOYSA-N 0.000 description 2
TUDTVAXRTPHZAJ-UHFFFAOYSA-N 1,3-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC(C=C)=C21 TUDTVAXRTPHZAJ-UHFFFAOYSA-N 0.000 description 2
SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
FTUDIUREWUBVKL-UHFFFAOYSA-N 1,8-bis(ethenyl)naphthalene Chemical compound C1=CC(C=C)=C2C(C=C)=CC=CC2=C1 FTUDIUREWUBVKL-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
JVXPEVSEOVECRV-UHFFFAOYSA-N 2,4-bis(ethenyl)-1-phenylbenzene Chemical group C=CC1=CC(C=C)=CC=C1C1=CC=CC=C1 JVXPEVSEOVECRV-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000010703 silicon Substances 0.000 description 2
230000003381 solubilizing effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
UWTUEMKLYAGTNQ-OWOJBTEDSA-N (e)-1,2-dibromoethene Chemical compound Br\C=C\Br UWTUEMKLYAGTNQ-OWOJBTEDSA-N 0.000 description 1
LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
GHITVUOBZBZMND-UHFFFAOYSA-N 1,3,5-tris(bromomethyl)benzene Chemical compound BrCC1=CC(CBr)=CC(CBr)=C1 GHITVUOBZBZMND-UHFFFAOYSA-N 0.000 description 1
FWFAJEYKHANIJP-UHFFFAOYSA-N 1,3,5-tris(ethenyl)naphthalene Chemical compound C1=CC=C(C=C)C2=CC(C=C)=CC(C=C)=C21 FWFAJEYKHANIJP-UHFFFAOYSA-N 0.000 description 1
SZEZDFQBIICMNO-UHFFFAOYSA-N 1,3-bis(ethenyl)-5-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC(C=C)=CC(C=C)=C1 SZEZDFQBIICMNO-UHFFFAOYSA-N 0.000 description 1
PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 1
IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-UHFFFAOYSA-N 0.000 description 1
WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
JHTICDZLXFNVKL-UHFFFAOYSA-N 1-ethenyl-4-(4-phenylbutyl)benzene Chemical compound C1=CC(C=C)=CC=C1CCCCC1=CC=CC=C1 JHTICDZLXFNVKL-UHFFFAOYSA-N 0.000 description 1
VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
PKADUYXVXKJWDI-UHFFFAOYSA-N 2,2-dibromodecan-3-one Chemical compound CCCCCCCC(=O)C(C)(Br)Br PKADUYXVXKJWDI-UHFFFAOYSA-N 0.000 description 1
MRFSSIQIRMXGQO-UHFFFAOYSA-N 2,4,6,9-tetrachlorodeca-3,7-diene Chemical compound CC(Cl)C=CC(Cl)CC(Cl)=CC(C)Cl MRFSSIQIRMXGQO-UHFFFAOYSA-N 0.000 description 1
UOPIOAUZQKSZRO-UHFFFAOYSA-N 2,4-dibromopentan-3-one Chemical compound CC(Br)C(=O)C(C)Br UOPIOAUZQKSZRO-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
KBKNKFIRGXQLDB-UHFFFAOYSA-N 2-fluoroethenylbenzene Chemical compound FC=CC1=CC=CC=C1 KBKNKFIRGXQLDB-UHFFFAOYSA-N 0.000 description 1
KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
DXFURPHVJQITAC-UHFFFAOYSA-N 4-benzyl-1-ethenyl-2-ethylbenzene Chemical compound C1=C(C=C)C(CC)=CC(CC=2C=CC=CC=2)=C1 DXFURPHVJQITAC-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
LNCNKWLTFCQSHO-UHFFFAOYSA-N C1=CC([Li])=CC=C1C1=CC=C([Li])C=C1 Chemical group C1=CC([Li])=CC=C1C1=CC=C([Li])C=C1 LNCNKWLTFCQSHO-UHFFFAOYSA-N 0.000 description 1
SSFGWDHVAMCZMG-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=C([Li])C2=C1 Chemical compound C1=CC=C2C([Li])=CC=C([Li])C2=C1 SSFGWDHVAMCZMG-UHFFFAOYSA-N 0.000 description 1
ZATOFRITFRPYBT-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=CC2=C1 Chemical compound C1=CC=C2C([Li])=CC=CC2=C1 ZATOFRITFRPYBT-UHFFFAOYSA-N 0.000 description 1
VIXXKNNHPJPCOF-UHFFFAOYSA-N C=1C=CC=CC=1C([Li])C([Li])CCCCCCC1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C([Li])C([Li])CCCCCCC1=CC=CC=C1 VIXXKNNHPJPCOF-UHFFFAOYSA-N 0.000 description 1
VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920000147 Styrene maleic anhydride Polymers 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
AVUYXHYHTTVPRX-UHFFFAOYSA-N Tris(2-methyl-1-aziridinyl)phosphine oxide Chemical compound CC1CN1P(=O)(N1C(C1)C)N1C(C)C1 AVUYXHYHTTVPRX-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
NTYDXFVCCCPXRG-UHFFFAOYSA-N [Li]C(C)(C)CC(C)(C)C Chemical compound [Li]C(C)(C)CC(C)(C)C NTYDXFVCCCPXRG-UHFFFAOYSA-N 0.000 description 1
FYOQEFGAZKEPGG-UHFFFAOYSA-N [Li]C1=CC=C(C)C=C1 Chemical compound [Li]C1=CC=C(C)C=C1 FYOQEFGAZKEPGG-UHFFFAOYSA-N 0.000 description 1
PYWOMDDOXZOOJZ-UHFFFAOYSA-N [Li]C1=CC=C([Li])C=C1 Chemical compound [Li]C1=CC=C([Li])C=C1 PYWOMDDOXZOOJZ-UHFFFAOYSA-N 0.000 description 1
LURCBQOZOZIVCW-UHFFFAOYSA-N [Li]C1CC([Li])C([Li])C([Li])C1 Chemical compound [Li]C1CC([Li])C([Li])C([Li])C1 LURCBQOZOZIVCW-UHFFFAOYSA-N 0.000 description 1
NTHIUKNPTBFSFZ-UHFFFAOYSA-N [Li]C1CC([Li])CC([Li])C1 Chemical compound [Li]C1CC([Li])CC([Li])C1 NTHIUKNPTBFSFZ-UHFFFAOYSA-N 0.000 description 1
CEAYJLIWHKSKBI-UHFFFAOYSA-N [Li]C1CCC([Li])CC1 Chemical compound [Li]C1CCC([Li])CC1 CEAYJLIWHKSKBI-UHFFFAOYSA-N 0.000 description 1
NTVIBFNHMURTMP-UHFFFAOYSA-N [Li]CC=CC[Li] Chemical compound [Li]CC=CC[Li] NTVIBFNHMURTMP-UHFFFAOYSA-N 0.000 description 1
LKSSGADQJSOVHJ-UHFFFAOYSA-N [Li]CCC([Li])CC([Li])CCC([Li])CC Chemical compound [Li]CCC([Li])CC([Li])CCC([Li])CC LKSSGADQJSOVHJ-UHFFFAOYSA-N 0.000 description 1
CYDIPADNXIGHGM-UHFFFAOYSA-N [Li]CCC([Li])CC[Li] Chemical compound [Li]CCC([Li])CC[Li] CYDIPADNXIGHGM-UHFFFAOYSA-N 0.000 description 1
XJPQDUFPQWLTMJ-UHFFFAOYSA-N [Li]CCC=CCCCC([Li])CC Chemical compound [Li]CCC=CCCCC([Li])CC XJPQDUFPQWLTMJ-UHFFFAOYSA-N 0.000 description 1
ZEDXYOJKIFJKHK-UHFFFAOYSA-N [Li]CCCCC1=CC=CC=C1 Chemical compound [Li]CCCCC1=CC=CC=C1 ZEDXYOJKIFJKHK-UHFFFAOYSA-N 0.000 description 1
JRBIPQPXIQFOLA-UHFFFAOYSA-N [Li]CCCCC1CCCCC1 Chemical compound [Li]CCCCC1CCCCC1 JRBIPQPXIQFOLA-UHFFFAOYSA-N 0.000 description 1
WZBHJENIKYQMHC-UHFFFAOYSA-N [Li]CCCCCCCCCCCCCCCCCCCC Chemical compound [Li]CCCCCCCCCCCCCCCCCCCC WZBHJENIKYQMHC-UHFFFAOYSA-N 0.000 description 1
QWFRFVPEFDDMQD-UHFFFAOYSA-N [Li]CCCCCCCCCC[Li] Chemical compound [Li]CCCCCCCCCC[Li] QWFRFVPEFDDMQD-UHFFFAOYSA-N 0.000 description 1
BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
RNUIRRIRPXUDDA-UHFFFAOYSA-N [Li]c1c2ccccc2c([Li])c2ccccc12 Chemical compound [Li]c1c2ccccc2c([Li])c2ccccc12 RNUIRRIRPXUDDA-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
JPHWRWNAPMZGNL-UHFFFAOYSA-N benzyl(tribromo)silane Chemical compound Br[Si](Br)(Br)CC1=CC=CC=C1 JPHWRWNAPMZGNL-UHFFFAOYSA-N 0.000 description 1
QNIBBHMNHNZZII-UHFFFAOYSA-N benzyl-tris(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)CC1=CC=CC=C1 QNIBBHMNHNZZII-UHFFFAOYSA-N 0.000 description 1
UDLNYNSUFIHIKN-UHFFFAOYSA-N bis(ethenyl)-diethylsilane Chemical compound CC[Si](CC)(C=C)C=C UDLNYNSUFIHIKN-UHFFFAOYSA-N 0.000 description 1
VOGRMWWTDBMKIF-UHFFFAOYSA-N bis(ethenyl)-methylphosphane Chemical compound C=CP(C)C=C VOGRMWWTDBMKIF-UHFFFAOYSA-N 0.000 description 1
GEKAWPIATFUQJW-UHFFFAOYSA-N bis(ethenyl)-phenylphosphane Chemical compound C=CP(C=C)C1=CC=CC=C1 GEKAWPIATFUQJW-UHFFFAOYSA-N 0.000 description 1
PMSZNCMIJVNSPB-UHFFFAOYSA-N bis(ethenyl)silicon Chemical compound C=C[Si]C=C PMSZNCMIJVNSPB-UHFFFAOYSA-N 0.000 description 1
239000006085 branching agent Substances 0.000 description 1
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 description 1
WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 description 1
HZGKWJZRNRZJIC-UHFFFAOYSA-N cyclohexyl-tris(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C1CCCCC1 HZGKWJZRNRZJIC-UHFFFAOYSA-N 0.000 description 1
MSLVEAIGPZQZBZ-UHFFFAOYSA-N cyclooctyl-bis(ethenyl)phosphane Chemical compound C=CP(C=C)C1CCCCCCC1 MSLVEAIGPZQZBZ-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
SZEZSRHDNMBIHZ-UHFFFAOYSA-N didodecyl-bis(ethenyl)silane Chemical compound CCCCCCCCCCCC[Si](C=C)(C=C)CCCCCCCCCCCC SZEZSRHDNMBIHZ-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
ULMVNJHMHWWTGW-UHFFFAOYSA-N dodecyl-bis(ethenyl)phosphane Chemical compound CCCCCCCCCCCCP(C=C)C=C ULMVNJHMHWWTGW-UHFFFAOYSA-N 0.000 description 1
229920001198 elastomeric copolymer Polymers 0.000 description 1
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WTTUTKBXMMXKBQ-UHFFFAOYSA-N lithium;stilbene Chemical compound C=1C=CC=CC=1C([Li])C([Li])C1=CC=CC=C1 WTTUTKBXMMXKBQ-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
HGZAZPZCKWFXNI-UHFFFAOYSA-N naphthalene-1,4,6-tricarbaldehyde Chemical compound O=CC1=CC=C(C=O)C2=CC(C=O)=CC=C21 HGZAZPZCKWFXNI-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
XUOPINLVSLTSMN-UHFFFAOYSA-N pentane-1,2,5-tricarbaldehyde Chemical compound C(C(CCCC=O)C=O)C=O XUOPINLVSLTSMN-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229920013730 reactive polymer Polymers 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
239000005052 trichlorosilane Substances 0.000 description 1
KXGOWZRHSOJOLF-UHFFFAOYSA-N triethyl benzene-1,3,5-tricarboxylate Chemical compound CCOC(=O)C1=CC(C(=O)OCC)=CC(C(=O)OCC)=C1 KXGOWZRHSOJOLF-UHFFFAOYSA-N 0.000 description 1
239000001069 triethyl citrate Substances 0.000 description 1
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
235000013769 triethyl citrate Nutrition 0.000 description 1
WPPVEXTUHHUEIV-UHFFFAOYSA-N trifluorosilane Chemical compound F[SiH](F)F WPPVEXTUHHUEIV-UHFFFAOYSA-N 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
PKRKCDBTXBGLKV-UHFFFAOYSA-N tris(ethenyl)-methylsilane Chemical compound C=C[Si](C)(C=C)C=C PKRKCDBTXBGLKV-UHFFFAOYSA-N 0.000 description 1
FUJPAQRDHMJPBB-UHFFFAOYSA-N tris(ethenyl)-phenylsilane Chemical compound C=C[Si](C=C)(C=C)C1=CC=CC=C1 FUJPAQRDHMJPBB-UHFFFAOYSA-N 0.000 description 1
OZHUWVSXUOMDDU-UHFFFAOYSA-N tris(ethenyl)phosphane Chemical compound C=CP(C=C)C=C OZHUWVSXUOMDDU-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
239000012855 volatile organic compound Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerization Catalysts (AREA)
Polymerisation Methods In General (AREA)

JP5077873A 1992-04-06 1993-04-05 アニオン重合調節剤 Pending JPH0641212A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/864,264 US5231153A (en)	1992-04-06	1992-04-06	Anionic polymerization of conjugated dienes modified with alkyltetrahydrofurfuryl ethers
US864264		1992-04-06

Publications (1)

Publication Number	Publication Date
JPH0641212A true JPH0641212A (ja)	1994-02-15

Family

ID=25342875

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5077873A Pending JPH0641212A (ja)	1992-04-06	1993-04-05	アニオン重合調節剤

Country Status (14)

Country	Link
US (3)	US5231153A (fr)
JP (1)	JPH0641212A (fr)
KR (1)	KR100258271B1 (fr)
AU (1)	AU655145B2 (fr)
BE (1)	BE1006548A3 (fr)
BR (1)	BR9301412A (fr)
CA (1)	CA2076148A1 (fr)
DE (1)	DE4311367A1 (fr)
ES (1)	ES2070075B1 (fr)
FR (1)	FR2689511B1 (fr)
GB (1)	GB2265902B (fr)
IT (1)	IT1261222B (fr)
MX (1)	MX9301873A (fr)
NL (1)	NL9300595A (fr)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5239009A (en) *	1991-10-16	1993-08-24	The Goodyear Tire & Rubber Company	High performance segmented elastomer
US5888992A (en) *	1992-03-11	1999-03-30	Narhex Limited	Polar substituted hydrocarbons
US6071895A (en) *	1992-03-11	2000-06-06	Narhex Limited	Polar-substituted hydrocarbons
JPH07504654A (ja) *	1992-03-11	1995-05-25	ナルヘックス　リミテッド	オキソ及びヒドロキシ置換炭化水素のアミン誘導体
MXPA93002392A (es)	1992-03-11	2005-02-04	Narhex Ltd	Derivados amino de hidrocarburos-oxo e hidroxi-substituidos.
US5231153A (en) *	1992-04-06	1993-07-27	The Goodyear Tire & Rubber Company	Anionic polymerization of conjugated dienes modified with alkyltetrahydrofurfuryl ethers
US5448003A (en) *	1992-04-06	1995-09-05	The Goodyear Tire & Rubber Company	Synthesis of rubbery polymer using anionic polymerization modifier
EP0609010B1 (fr) *	1993-01-29	2000-03-15	Bridgestone Corporation	Préparation d'un polymère ou d'un copolymère d'une dioléfine et composition contenant ce polymère ou ce copolymère
US5470929A (en) *	1993-03-29	1995-11-28	The Goodyear Tire & Rubber Company	Process for synthesizing styrene-isoprene rubber
US5359016A (en) *	1993-03-29	1994-10-25	The Goodyear Tire & Rubber Company	Process for the synthesis of styrene-isoprene rubber
KR100332859B1 (ko) *	1993-07-28	2002-11-23	롬 앤드 하스 캄파니	밀도가높고,표면적이넓은흡착제
US5774252A (en) *	1994-01-07	1998-06-30	Texas Instruments Incorporated	Membrane device with recessed electrodes and method of making
US5623035A (en) *	1995-07-21	1997-04-22	The Goodyear Tire & Rubber Company	Process for the synthesis of rubbery polymers
US6231783B1 (en)	1995-11-14	2001-05-15	Massachusetts Institute Of Technology	Replacement solvents for use in chemical synthesis
US5728782A (en) *	1996-12-06	1998-03-17	Union Carbide Chemicals & Plastics Technology Corporation	Gas phase anionic polymerization of dienes and vinyl-substituted aromatic compounds
IT1289605B1 (it) *	1997-01-30	1998-10-15	Enichem Spa	Copolimerizzazione anionica di dieni coniugati e vinil areni in presenza di alchil eteri del tetraidropiranil metanolo
CA2282955A1 (fr)	1998-10-13	2000-04-13	The Goodyear Tire & Rubber Company	Compose pour bande de roulement
US6140434A (en) *	1999-01-08	2000-10-31	The Goodyear Tire & Rubber Company	Synthesis of high vinyl rubber
CN100509879C (zh) *	2001-07-16	2009-07-08	米其林技术公司	含有环乙烯基单元的二烯高弹体及其制备工艺
US6583244B1 (en) *	2001-10-31	2003-06-24	The Goodyear Tire & Rubber Company	Synthesis of rubber having a low vinyl content
ITMI20060385A1 (it) *	2006-03-03	2007-09-04	Polimeri Europa Spa	Procedimento in continuo per la preparazione di copolimeri randon dieni coniugati-vinil areni
ITMI20071210A1 (it) *	2007-06-15	2008-12-16	Polimeri Europa Spa	Procedimento per la idrogenazione parziale di copolimeri random vinil arene-diene coniugato
CN101962423B (zh) *	2009-07-22	2012-11-28	中国石油化工股份有限公司	一种三元共聚橡胶的制备方法及其应用
BR112012015120B1 (pt)	2009-12-22	2020-07-21	Bridgestone Corporation	composição de modificador de vinila melhorada e processos para a utilização da mesma
CN101845109B (zh) *	2010-04-16	2011-11-09	北京化工大学	一种含氮氧杂原子的不对称结构调节剂的应用
RU2569674C2 (ru) *	2010-10-28	2015-11-27	Чайна Петролеум & Кемикал Корпорейшн	Гетерогенная каталическая композиция для полимеризации изопропена, способ ее получения и применения
ITMI20111198A1 (it) *	2011-06-29	2012-12-30	Polimeri Europa Spa	"procedimento per la preparazione di copolimeri di 1,3-butadiene e stirene e loro impiego in composizioni elastomeriche vulcanizzabili"
CN102964318A (zh) *	2012-11-11	2013-03-13	新疆科源化工有限公司	Ete副产物的回收精制方法
CN105503784B (zh) *	2015-12-15	2018-03-20	尤学民	一种工业化超声波反应生产四氢糠醇乙醚的方法及装置
BR112019000021B1 (pt)	2016-09-09	2023-03-28	Dynasol Elastómeros, S.A. De C.V	Sistemas modificadores polares para copolimerização em bloco com alto conteúdo de vinila, copolímero em bloco, e seu processo de produção
JP7249349B2 (ja) *	2017-12-27	2023-03-30	ボレアリスエージー	チーグラー・ナッタ触媒及びその調製
EA202091168A1 (ru)	2017-12-28	2020-11-24	Бореалис Аг	Катализатор и его получение
US11542355B2 (en)	2018-10-18	2023-01-03	Dynasol Elastómeros, S.A. De C.V.	Polar modifier systems for high vinyl block copolymerization
CN115785525B (zh) *	2021-09-10	2024-03-26	中国石油化工股份有限公司	结构调节剂组合物和液体状的三元共聚物及其制备方法和应用

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3639380A (en) *	1968-01-24	1972-02-01	Lithium Corp	Preparation of microcrystalline waxes
GB1311856A (en) *	1969-08-07	1973-03-28	Int Synthetic Rubber	Graft copolymerisation process
US3847883A (en) *	1970-07-23	1974-11-12	Gulf Research Development Co	Method of preparing polymers utilizing as catalysts hydrocarbon-soluble complexes of an organomagnesium compound with a group i organometallic compound
JPS5221548B2 (fr) *	1971-11-22	1977-06-11
JPS56149413A (en) *	1980-04-22	1981-11-19	Japan Synthetic Rubber Co Ltd	Production of styrene/butadiene copolymer
JPS58154703A (ja) *	1982-03-09	1983-09-14	Daicel Chem Ind Ltd	光学活性な高分子の合成方法
DE3310118A1 (de) *	1982-05-28	1983-12-01	Chemische Werke Hüls AG, 4370 Marl	Vulkanisierbare massen
US4429090A (en) *	1983-03-09	1984-01-31	The Firestone Tire & Rubber Company	Catalyst containing oligomeric oxolanyl alkane modifiers and process for the production of polymers having increased 1,2-microstructure
US4429091A (en) *	1983-03-09	1984-01-31	The Firestone Tire & Rubber Company	Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators
SU1131885A1 (ru) *	1983-04-18	1984-12-30	Предприятие П/Я А-7629	Способ получени 1,2-полибутадиена
US4761456A (en) *	1985-06-17	1988-08-02	The Dow Chemical Company	Process for metallating nonconjugated diene-containing ethylene polymers and graft polymers prepared therefrom
ZA865707B (en) *	1985-09-03	1987-03-25	Firestone Tire & Rubber Co	Oligomeric oxolanyl alkanes as randomizers for copolymerization
US4647635A (en) *	1986-03-25	1987-03-03	The Firestone Tire & Rubber Company	Initiator systems for polymerization of 1,3-dienes or copolymers containing 1,3-dienes
DE3707434A1 (de) *	1986-05-31	1987-12-03	Huels Chemische Werke Ag	Polyisoprene mit einem hohen anteil von 1,2- und 3,4-struktureinheiten, verfahren zu ihrer herstellung und ihre verwendung
US4696986A (en) *	1986-08-12	1987-09-29	The Goodyear Tire & Rubber Company	Modifier for lithium catalysts
US4933401A (en) *	1988-02-26	1990-06-12	Japan Synthetic Rubber Co., Ltd.	Catalyst composition for polymerization of conjugated diene and process for producing conjugated diene polymer
US5047483A (en) *	1988-06-29	1991-09-10	The Goodyear Tire & Rubber Company	Pneumatic tire with tread of styrene, isoprene, butadiene rubber
JP2730163B2 (ja) *	1989-04-07	1998-03-25	日本合成ゴム株式会社	高トランス低ビニル共役ジエン系重合体の製造方法
US5112919A (en) *	1989-10-30	1992-05-12	Union Carbide Chemicals & Plastics Technology Corporation	Solid feeding of silane crosslinking agents into extruder
US5112929A (en) *	1991-04-05	1992-05-12	Bridgestone Corporation	Oxolanyl cyclic acetals as anionic polymerization modifiers
US5231153A (en) *	1992-04-06	1993-07-27	The Goodyear Tire & Rubber Company	Anionic polymerization of conjugated dienes modified with alkyltetrahydrofurfuryl ethers

1992
- 1992-04-06 US US07/864,264 patent/US5231153A/en not_active Expired - Lifetime
- 1992-08-14 CA CA002076148A patent/CA2076148A1/fr not_active Abandoned
1993
- 1993-03-31 BE BE9300317A patent/BE1006548A3/fr not_active IP Right Cessation
- 1993-03-31 MX MX9301873A patent/MX9301873A/es not_active IP Right Cessation
- 1993-04-01 ES ES09300674A patent/ES2070075B1/es not_active Expired - Fee Related
- 1993-04-02 BR BR9301412A patent/BR9301412A/pt not_active IP Right Cessation
- 1993-04-02 KR KR1019930005597A patent/KR100258271B1/ko not_active Expired - Fee Related
- 1993-04-05 JP JP5077873A patent/JPH0641212A/ja active Pending
- 1993-04-05 FR FR9304005A patent/FR2689511B1/fr not_active Expired - Fee Related
- 1993-04-05 AU AU36725/93A patent/AU655145B2/en not_active Ceased
- 1993-04-05 GB GB9307039A patent/GB2265902B/en not_active Expired - Fee Related
- 1993-04-05 IT ITRM930208A patent/IT1261222B/it active IP Right Grant
- 1993-04-05 NL NL9300595A patent/NL9300595A/nl active Search and Examination
- 1993-04-06 DE DE4311367A patent/DE4311367A1/de not_active Withdrawn
- 1993-04-08 US US08/043,712 patent/US5300599A/en not_active Expired - Lifetime
- 1993-07-22 US US08/094,736 patent/US5336739A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
GB2265902A (en)	1993-10-13
MX9301873A (es)	1993-10-01
GB2265902B (en)	1996-04-17
FR2689511B1 (fr)	1995-07-28
US5300599A (en)	1994-04-05
ES2070075A1 (es)	1995-05-16
CA2076148A1 (fr)	1993-10-07
ITRM930208A1 (it)	1994-10-05
ITRM930208A0 (it)	1993-04-05
US5336739A (en)	1994-08-09
BR9301412A (pt)	1993-10-13
KR100258271B1 (ko)	2000-06-01
KR930021663A (ko)	1993-11-22
NL9300595A (nl)	1993-11-01
DE4311367A1 (de)	1993-10-07
FR2689511A1 (fr)	1993-10-08
BE1006548A3 (fr)	1994-10-11
GB9307039D0 (en)	1993-05-26
US5231153A (en)	1993-07-27
AU3672593A (en)	1993-10-14
ES2070075B1 (es)	1996-02-01
AU655145B2 (en)	1994-12-01
IT1261222B (it)	1996-05-09

Publication	Publication Date	Title
KR100258271B1 (ko)	2000-06-01	음이온성 중합 개질제
EP0282437B1 (fr)	1993-03-03	Procédé de polymérisation
US5753579A (en)	1998-05-19	Trans microstructure directing initiator system
JP4480321B2 (ja)	2010-06-16	ＩＩａ族金属含有触媒系
US5100965A (en)	1992-03-31	Process for synthesizing high trans polymers
US4696986A (en)	1987-09-29	Modifier for lithium catalysts
JPH10306114A (ja)	1998-11-17	低いビニル微細構造を有するランダムトランスｓｂｒ
EP1892125A2 (fr)	2008-02-27	Système catalyseur contenant des amines et procédés d'utilisation correspondant
US6043321A (en)	2000-03-28	Asymmetrical tin-coupled rubbery polymers
US5448003A (en)	1995-09-05	Synthesis of rubbery polymer using anionic polymerization modifier
JP3877836B2 (ja)	2007-02-07	テトラヒドロピラニルメタノールのアルキルエーテルの存在下での共役ジエンとビニルアレーンのアニオン共重合
GB2354243A (en)	2001-03-21	Coupled rubbery polymers containing tin and silicon
JP4308956B2 (ja)	2009-08-05	錫でカップリングされたゴム状ポリマーの製造方法
GB2322133A (en)	1998-08-19	Asymmetrical tin-coupled rubbery polymers
US6075095A (en)	2000-06-13	Process for making tin-coupled rubbery polymers
GB2368069A (en)	2002-04-24	Dialkylsiloxane-diene-dialkylsiloxane triblock rubber
JPS6223961B2 (fr)	1987-05-26
US7825202B2 (en)	2010-11-02	Potassium based catalyst systems for synthesizing rubbery polymers
US5739182A (en)	1998-04-14	Stabilization of tin-coupled polymers
EP1967532A1 (fr)	2008-09-10	Polymères caoutchouteux contenant des agents de couplage en étain et composés de caoutchouc l'incluant
GB2354244A (en)	2001-03-21	Stabilising tin-coupled rubbery polymers with styrene